Reactions of Malononitrile with Cross-conjugated Dienone Derivatives of Cyclohexane. Synthesis of Substituted Partially Hydrogenated Quinoline- and Chromenecarbonitriles

The condensation of malononitrile with unsymmetrical dienones of the cyclohexane series under basic conditions selectively afforded substituted tetrahydroquinolinecarbonitriles. The reaction of 2,6-bis-(3-nitrophenylmethylidene)cyclohexan-1-one with malononitrile under similar conditions led to the...

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Published in:Russian journal of organic chemistry 2019-07, Vol.55 (7), p.995-998
Main Authors: Vasilkova, N. O., Kalugina, A. S., Nikulin, A. V., Krivenko, A. P.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Cyclohexane
Malononitrile
NMR
Nuclear magnetic resonance
Organic Chemistry
Quinoline
Selectivity
Substitutes
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description The condensation of malononitrile with unsymmetrical dienones of the cyclohexane series under basic conditions selectively afforded substituted tetrahydroquinolinecarbonitriles. The reaction of 2,6-bis-(3-nitrophenylmethylidene)cyclohexan-1-one with malononitrile under similar conditions led to the formation of substituted tetrahydrochromenecarbonitrile. Factors determining the reaction direction and selectivity were discussed. The structure of the newly synthesized compounds was confirmed by IR and 1 H NMR spectra.
doi_str_mv 10.1134/S1070428019070145
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subjects Chemistry
Chemistry and Materials Science
Cyclohexane
Malononitrile
NMR
Nuclear magnetic resonance
Organic Chemistry
Quinoline
Selectivity
Substitutes
title Reactions of Malononitrile with Cross-conjugated Dienone Derivatives of Cyclohexane. Synthesis of Substituted Partially Hydrogenated Quinoline- and Chromenecarbonitriles
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